Dallas (Love Field) (DAL)to
Chicago (O'Hare) (ORD)Las Vegas (LAS)to
Chicago (O'Hare) (ORD)Tampa (TPA)to
Chicago (O'Hare) (ORD)Nashville (BNA)to
Chicago (O'Hare) (ORD)Orlando (MCO)to
Chicago (O'Hare) (ORD)Denver (DEN)to
Chicago (O'Hare) (ORD)Phoenix (PHX)to
Chicago (O'Hare) (ORD)San Francisco (SFO)to
Chicago (O'Hare) (ORD)Washington, D.C. (Reagan National) (DCA)to
Chicago (O'Hare) (ORD)Houston (Hobby) (HOU)to
Chicago (O'Hare) (ORD)San Diego (SAN)to
Chicago (O'Hare) (ORD)Baltimore/Washington (BWI)to
Chicago (O'Hare) (ORD)Austin (AUS)to
Chicago (O'Hare) (ORD)Kansas City (MCI)to
Chicago (O'Hare) (ORD)Atlanta (ATL)to
Chicago (O'Hare) (ORD)Oakland (OAK)to
Chicago (O'Hare) (ORD)New York (LaGuardia) (LGA)to
Chicago (O'Hare) (ORD)Fort Lauderdale (FLL)to
Chicago (O'Hare) (ORD)San Jose, CA (SJC)to
Chicago (O'Hare) (ORD)Los Angeles (LAX)to
Chicago (O'Hare) (ORD)*Fares displayed have been collected within the last 24 hours and may no longer be available at time of booking. Additional fees and charges for optional products and services may apply. Modifying this information may result in a different fare. To find the most updated fare, please visit Southwest.com. Fares listed are Basic, which are subject to additional terms and conditions.
Book your next flight to Chicago with Southwest Airlines and see why the Windy City is one of the most dynamic destinations in the U.S. Learn more about the Southwest Experience and start planning your Chicago getaway today.
Flying into Chicago O'Hare with Southwest Airlines
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† Weekly flights based on DOT published schedule average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.
‡ Weekday flights based on DOT published schedule average flights Monday through Friday between 9/1/2025 and 9/30/2025.
§ Nonstop flights based on DOT published schedule average flights Saturday through Sunday between 9/1/2025 and 9/30/2025.
St. Louis (STL)to
One-way
Choice
Cleveland (CLE)to
One-way
Choice
Columbus (CMH)to
One-way
Choice
Dallas (Love Field) (DAL)to
One-way
Basic
Orlando (MCO)to
One-way
Basic
Tampa (TPA)to
One-way
Basic
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